Andrew's gun-running friend

The prince's coterie includes a Libyan caught importing a machinegun into Paris

Prince Andrew has been befriended by a Libyan-born businessman who in 2005 was convicted of buying a machine gun and trying to smuggle it into France. On a private visit to Tunisia earlier this month Andrew was shown around by his friend Tarek Kaituni, who has a house there. He also met Colonel Muammar Gadaffi, the Libyan president.

Andrew and Kaituni, who were introduced by a Middle Eastern sheikh, are regularly seen together on the European party circuit and last year both attended a lavish VIP hunting trip in Kazakhstan hosted by the country's president.

Andrew's choice of associates has come under scrutiny since The Sunday Times revealed earlier this year that he had sold Sunninghill Park, his former home in Berkshire, for more than £3m over the asking price to senior Kazakh figures. It has since been left to rot.